Business Operations & Chief of Staff

Coinscapture; Northern (KY); Hybrid; USD 150,000 - 210,000; Full time

Job summary

Waymark is seeking a Director & Chief of Staff to lead strategic planning and management, internal communications, and core operating processes as the company scales. You will partner with the CEO and executive team to set direction, align roadmaps, and drive cross-functional execution.

This role blends strategic leadership with hands-on operations, owning annual/quarterly planning, executive rhythms, and a unified operating infrastructure to support Waymark’s growth and performance.

Responsibilities

• Strategic Planning & Management: refresh multi-year vision, translate strategy into goals, roadmaps and resource decisions.
• OKR/goal-setting: drive objective setting, progress tracking and corrective actions across teams.
• Executive rhythm: manage leadership meetings, decisions, quarterly reviews and offsites.
• Insight & risk: provide analysis on performance, risks and recommendations.
• Cross-functional initiatives: lead high-priority programs and ambiguous projects for growth.
• Internal Communications: own strategy and calendar, ensure employee understanding of direction and progress.
• All-hands and leadership comms: plan events, craft announcements, and prepare exec decks.
• Board narratives: assist in developing quarterly board materials.
• Decision-making infrastructure: own memo process, approvals, vendor reviews with Finance/Legal/Security.
• Identify process friction and redesign workflows with owners to drive closure.

Job description

About Waymark

Waymark is a team of healthcare providers, technologists, and builders whose mission is to bring the best healthcare to people with Medicaid benefits. Guided by the communities we serve, we bring support and technology-enabled care to help primary care providers keep Medicaid patients healthy. We are building the tools and designing an approach to enable care to reach the patients who can benefit most.

Our core values

• We are bold builders, believing that the greatest challenges in care delivery can be solved when we harness the power of community and technology.
• We are humble learners, seeking feedback and perspectives different from our own, and welcome challenges to our conclusions.
• We experiment to improve, actively seeking data to inform decisions and to assess our own performance.
• We act with focused urgency, our commitment to our mission drives us to tirelessly pursue results.

About the Role

The Business

Operations

Director & Chief of Staff is a senior contributor responsible for how Waymark plans, communicates, and operates as a company.

Reporting directly to the Head of Operations and working closely with the CEO and Executive Leadership Team, this leader owns three interconnected mandates: the company's strategic planning and management system, company and internal communications, and the development of the business processes that keep a scaling organization coordinated and accountable.

This role blends the altitude of a strategy leader with the hands-on execution of an operator. You will run the top-level goal-setting processes through which the company sets direction - including company-level planning and performance reviews - and the communications through which that direction reaches every employee. You will design and continuously improve the operating infrastructure the company runs on, from decision-making frameworks to cross-functional workflows. And as a trusted thought partner and proxy for executive leadership, you will take on the ambiguous, high-stakes problems that don't fit neatly within any single function.

Responsibilities

• Strategic Planning & Management
• Own the company's strategic planning system: refreshing the multi year strategic vision; translating company strategy into clear goals, priorities, and resource allocation decisions; designing and running company-level annual and quarterly planning cycles, rolling up department-level roadmaps and driving key prioritization decisions.
• Drive the OKR / goal-setting process end to end - objective setting, results consolidation, progress monitoring, and corrective action - ensuring clarity, consistency, and accountability across all teams.
• Run the executive operating rhythm: leadership team meeting cadence and agendas, decision tracking, quarterly business reviews, and executive offsites.
• Provide executive leadership with insight and analysis on company performance, surfacing risks, trade-offs, and recommendations to inform key decisions.
• Serve as a versatile utility player for the executive team: lead high-priority cross-functional initiatives and special projects, bringing structure and momentum to ambiguous problem spaces critical to Waymark's growth.
• Company & Internal Communications
• Own the company's internal communications strategy and calendar, ensuring employees understand company direction, priorities, progress, and key decisions.
• Plan and produce all-company meetings, leadership communications, and company events - narrative, content, and logistics.
• Draft and edit high-stakes executive communications: company-wide announcements, strategy narratives, decision memos, and executive presentations.
• Co-lead the development of board narrative / decks for quarterly meetings.
• Act as a conduit between the executive team and the broader organization - cascading decisions and strategic direction downward and channeling feedback, questions, and early signals of misalignment upward.
• Ensure follow-through on decisions and commitments made in executive forums, routing actions to the right owners and driving them to closure.
• Business Process Development
• Design, implement, and continuously improve the core operating processes that keep the company coordinated as it scales - planning, reporting, decision-making, administration, and cross-functional coordination workflows.
• Own the company's decision-making infrastructure, including decision-memo process, approval workflows, and vendor and procurement review, in partnership with Partnerships, Finance, Legal, and Security.
• Identify organizational friction, process gaps, and duplicated effort; partner with functional leaders to redesign workflows and clarify ownership.
• Sustain...